JP6419800B2 - Ｎｍｄａ受容体活性の調節因子としてのチアゾロピリミジノン - Google Patents

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Publication number

JP6419800B2

JP6419800B2 JP2016521943A JP2016521943A JP6419800B2 JP 6419800 B2 JP6419800 B2 JP 6419800B2 JP 2016521943 A JP2016521943 A JP 2016521943A JP 2016521943 A JP2016521943 A JP 2016521943A JP 6419800 B2 JP6419800 B2 JP 6419800B2

Authority

JP

Japan

Prior art keywords

methyl

thiazolo

pyrimidin

trifluoromethyl

oxo

Prior art date

2013-10-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 230000000694 effects Effects 0.000 title claims description 17
• 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 title description 26
• 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 title description 4
• AKDQOJPOLRMVMF-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine 3-oxide Chemical compound N1=CN=C2S(=O)C=NC2=C1 AKDQOJPOLRMVMF-UHFFFAOYSA-N 0.000 title description 4
• -1 —CF 3 Chemical group 0.000 claims description 334
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 268
• 150000001875 compounds Chemical class 0.000 claims description 191
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 162
• 125000000217 alkyl group Chemical group 0.000 claims description 145
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 117
• 125000001424 substituent group Chemical group 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 103
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 73
• 229910052799 carbon Inorganic materials 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• ILJHFJMCUBAZLV-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(hydroxymethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CO)c(C)sc2n1)c1ccc(F)cc1 ILJHFJMCUBAZLV-UHFFFAOYSA-N 0.000 claims description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
• 125000001153 fluoro group Chemical group F* 0.000 claims description 52
• 125000005843 halogen group Chemical group 0.000 claims description 52
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 42
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 41
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 36
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 35
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
• LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 32
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 29
• 201000010099 disease Diseases 0.000 claims description 28
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 25
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 19
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 13
• 125000001425 triazolyl group Chemical group 0.000 claims description 13
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 11
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
• CJDCZVBFZVDWJU-XHDPSFHLSA-N 7-[(4-fluorophenoxy)methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(COc3ccc(F)cc3)cc(=O)n2c1[C@@H]1C[C@H]1CO CJDCZVBFZVDWJU-XHDPSFHLSA-N 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 125000003566 oxetanyl group Chemical group 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• UQCKKOVHIYNXCG-UHFFFAOYSA-N 3-(1,3-dihydroxypropyl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C(O)CCO)c(C)sc2n1)c1ccc(F)cc1 UQCKKOVHIYNXCG-UHFFFAOYSA-N 0.000 claims description 4
• YBHLUMHIQAJIRJ-UHFFFAOYSA-N 7-[(3-cyano-2-fluorophenyl)methyl]-N-ethyl-6-fluoro-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1csc2nc(Cc3cccc(C#N)c3F)c(F)c(=O)n12 YBHLUMHIQAJIRJ-UHFFFAOYSA-N 0.000 claims description 4
• NANCFADVIHSXEF-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(2-hydroxyethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CCO)c(C)sc2n1)c1ccc(F)cc1 NANCFADVIHSXEF-UHFFFAOYSA-N 0.000 claims description 4
• OZBUYWSMWLUMTI-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(3-hydroxypropyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CCCO)c(C)sc2n1)c1ccc(F)cc1 OZBUYWSMWLUMTI-UHFFFAOYSA-N 0.000 claims description 4
• KKKOYGPZMYVPMY-UHFFFAOYSA-N 7-[[3-(difluoromethyl)-2-fluorophenyl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cccc(C(F)F)c3F)cc(=O)n12 KKKOYGPZMYVPMY-UHFFFAOYSA-N 0.000 claims description 4
• TUTMPJHNKVBVCA-UHFFFAOYSA-N 7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3C3CC3)C(F)(F)F)cc(=O)n2c1-c1cncnc1 TUTMPJHNKVBVCA-UHFFFAOYSA-N 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 4
• QRQSDYJWBHKWOT-MLGOLLRUSA-N 2-[(1S,2R)-2-[7-[(4-fluorophenoxy)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropyl]acetonitrile Chemical compound FC1=CC=C(OCC=2N=C3N(C(C=2)=O)C(=C(S3)C)[C@H]2[C@@H](C2)CC#N)C=C1 QRQSDYJWBHKWOT-MLGOLLRUSA-N 0.000 claims description 3
• BYANGMQBUROMBT-UHFFFAOYSA-N 2-[7-[(4-fluorophenoxy)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound CNC(=O)Cc1c(C)sc2nc(COc3ccc(F)cc3)cc(=O)n12 BYANGMQBUROMBT-UHFFFAOYSA-N 0.000 claims description 3
• IJJLPQYNAHVCLI-UHFFFAOYSA-N 2-cyclopropyl-N-ethyl-7-[(4-fluorophenoxy)methyl]-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(sc2nc(COc3ccc(F)cc3)cc(=O)n12)C1CC1 IJJLPQYNAHVCLI-UHFFFAOYSA-N 0.000 claims description 3
• NTFBVXXJEOVXSU-GOEBONIOSA-N 3-[[3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound Cc1sc2nc(Cc3cccc(c3)C#N)cc(=O)n2c1[C@@H]1C[C@H]1CO NTFBVXXJEOVXSU-GOEBONIOSA-N 0.000 claims description 3
• OCQXYYLFUPOYKW-UHFFFAOYSA-N 7-[(3-cyano-2-fluorophenyl)methyl]-6-fluoro-N,N-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CN(C)C(=O)c1csc2nc(Cc3cccc(C#N)c3F)c(F)c(=O)n12 OCQXYYLFUPOYKW-UHFFFAOYSA-N 0.000 claims description 3
• ITXUBEXPFBRJMB-UHFFFAOYSA-N 7-[(4-fluorophenoxy)methyl]-2-methyl-3-(2-methylcyclopropyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC1CC1c1c(C)sc2nc(COc3ccc(F)cc3)cc(=O)n12 ITXUBEXPFBRJMB-UHFFFAOYSA-N 0.000 claims description 3
• VSOVXQSIUAWQCO-UHFFFAOYSA-N 7-[(4-fluorophenoxy)methyl]-3-(3-hydroxypropyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(COc3ccc(F)cc3)cc(=O)n2c1CCCO VSOVXQSIUAWQCO-UHFFFAOYSA-N 0.000 claims description 3
• CJDCZVBFZVDWJU-IAQYHMDHSA-N 7-[(4-fluorophenoxy)methyl]-3-[(1R,2S)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(COc3ccc(F)cc3)cc(=O)n2c1[C@@H]1C[C@@H]1CO CJDCZVBFZVDWJU-IAQYHMDHSA-N 0.000 claims description 3
• LXAAHNSAKBLLKC-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(2,2,2-trifluoro-1-hydroxyethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C(O)C(F)(F)F)c(C)sc2n1)c1ccc(F)cc1 LXAAHNSAKBLLKC-UHFFFAOYSA-N 0.000 claims description 3
• JGXAVXQOGSNNBP-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)C(F)(F)F)c1ccc(F)cc1 JGXAVXQOGSNNBP-UHFFFAOYSA-N 0.000 claims description 3
• AKNJXYTVPQMGQF-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-morpholin-4-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(N3CCOCC3)c(C)sc2n1)c1ccc(F)cc1 AKNJXYTVPQMGQF-UHFFFAOYSA-N 0.000 claims description 3
• FTVBSUKOMCKIJE-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cncnc1)c1ccc(F)cc1 FTVBSUKOMCKIJE-UHFFFAOYSA-N 0.000 claims description 3
• HPIRRFGALNDNPI-COKTVNPCSA-N 7-[1-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]ethyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC(c1cc(=O)n2c([C@@H]3C[C@H]3CO)c(C)sc2n1)n1nc(cc1C1CC1)C(F)(F)F HPIRRFGALNDNPI-COKTVNPCSA-N 0.000 claims description 3
• KCPLXGPUJPQMNS-GXFFZTMASA-N 7-[[3-(2-hydroxyethyl)-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(CCO)cc3C(F)(F)F)cc(=O)n2c1[C@@H]1C[C@H]1CO KCPLXGPUJPQMNS-GXFFZTMASA-N 0.000 claims description 3
• QFIKJXWLQXBBNF-CMPLNLGQSA-N 7-[[3-cyclopropyl-4-fluoro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=NN(C(=C1F)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)[C@H]1[C@@H](C1)CO QFIKJXWLQXBBNF-CMPLNLGQSA-N 0.000 claims description 3
• RIKRWRLJRVUIHU-UHFFFAOYSA-N 7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cn3nc(cc3C(F)(F)F)C3CC3)cc(=O)n12 RIKRWRLJRVUIHU-UHFFFAOYSA-N 0.000 claims description 3
• DVMFSLLMBDNTRU-GXFFZTMASA-N 7-[[5-(2-hydroxyethyl)-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound OCCC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)[C@H]1[C@@H](C1)CO)C(F)(F)F DVMFSLLMBDNTRU-GXFFZTMASA-N 0.000 claims description 3
• IHEVCDMBKVGUDX-UHFFFAOYSA-N 7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cn3nc(cc3C3CC3)C(F)(F)F)cc(=O)n12 IHEVCDMBKVGUDX-UHFFFAOYSA-N 0.000 claims description 3
• ZNFJTEWGOBYOJH-CMPLNLGQSA-N 7-[[5-cyclopropyl-4-fluoro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=C(C(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)[C@H]1[C@@H](C1)CO)C(F)(F)F)F ZNFJTEWGOBYOJH-CMPLNLGQSA-N 0.000 claims description 3
• YHCWGQRPOKYADK-UHFFFAOYSA-N N-(cyanomethyl)-7-[(4-fluorophenoxy)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)CNC(=O)C1=C(SC=2N1C(C=C(N=2)COC1=CC=C(C=C1)F)=O)C YHCWGQRPOKYADK-UHFFFAOYSA-N 0.000 claims description 3
• IMYRBXZVXWDWQM-UHFFFAOYSA-N N-ethyl-7-[(2-ethyl-4,5-difluorophenyl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cc(F)c(F)cc3CC)cc(=O)n12 IMYRBXZVXWDWQM-UHFFFAOYSA-N 0.000 claims description 3
• XVXXBLCNXUKTRD-UHFFFAOYSA-N N-ethyl-7-[1-[2-fluoro-3-(trifluoromethyl)phenyl]ethyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)NC(=O)C1=C(SC=2N1C(C=C(N=2)C(C)C1=C(C(=CC=C1)C(F)(F)F)F)=O)C XVXXBLCNXUKTRD-UHFFFAOYSA-N 0.000 claims description 3
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
• 125000002346 iodo group Chemical group I* 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• PWZVRYNFWVGCLW-DZGCQCFKSA-N 2-fluoro-3-[[3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound Cc1sc2nc(Cc3cccc(C#N)c3F)cc(=O)n2c1[C@@H]1C[C@H]1CO PWZVRYNFWVGCLW-DZGCQCFKSA-N 0.000 claims description 2
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 2
• BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims description 2
• AICPBWWXLHAMLC-UHFFFAOYSA-N 3-(ethoxymethyl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCOCc1c(C)sc2nc(CN(CC)c3ccc(F)cc3)cc(=O)n12 AICPBWWXLHAMLC-UHFFFAOYSA-N 0.000 claims description 2
• GEXCYHCLUSCUOK-UHFFFAOYSA-N 3-[7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanamide Chemical compound CCN(Cc1cc(=O)n2c(CCC(N)=O)c(C)sc2n1)c1ccc(F)cc1 GEXCYHCLUSCUOK-UHFFFAOYSA-N 0.000 claims description 2
• MEAZWVIEZHZOCZ-UHFFFAOYSA-N 3-[7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanenitrile Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CCC#N MEAZWVIEZHZOCZ-UHFFFAOYSA-N 0.000 claims description 2
• ORMJLGRRAOIFAS-UHFFFAOYSA-N 3-[[3-(2-cyanocyclopropyl)-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound Cc1sc2nc(Cc3cccc(c3)C#N)cc(=O)n2c1C1CC1C#N ORMJLGRRAOIFAS-UHFFFAOYSA-N 0.000 claims description 2
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• CZRZPVLQPNBJGL-UHFFFAOYSA-N 3-acetyl-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C(C)=O)c(C)sc2n1)c1ccc(F)cc1 CZRZPVLQPNBJGL-UHFFFAOYSA-N 0.000 claims description 2
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• MHTKPFBYBNSRKL-UHFFFAOYSA-N 7-[(3-cyclopropyl-2-fluorophenyl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cccc(C4CC4)c3F)cc(=O)n12 MHTKPFBYBNSRKL-UHFFFAOYSA-N 0.000 claims description 2
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
• AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
• 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 2
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
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• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 8
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• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
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• YISSQNWTPFMKED-UHFFFAOYSA-N 2-[2-methyl-7-[[1-methyl-4-(trifluoromethyl)imidazol-2-yl]methyl]-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound CC1=C(N2C(=NC(=CC2=O)CC=2N(C=C(N=2)C(F)(F)F)C)S1)C1C(C1)C#N YISSQNWTPFMKED-UHFFFAOYSA-N 0.000 claims 1
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• FVIKKTYAURSMJU-UHFFFAOYSA-N 2-[7-[(3-cyclopropyl-2-fluorophenyl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC(=O)NC)F FVIKKTYAURSMJU-UHFFFAOYSA-N 0.000 claims 1
• JKUYTYAHBSWWHN-UHFFFAOYSA-N 2-[7-[(4,5-difluoro-2-methoxyphenyl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound FC1=CC(=C(C=C1F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N)OC JKUYTYAHBSWWHN-UHFFFAOYSA-N 0.000 claims 1
• HMWUHTMLJDKVTD-UHFFFAOYSA-N 2-[7-[(4-chloro-1-methylpyrazol-3-yl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC=1C(=NN(C=1)C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N HMWUHTMLJDKVTD-UHFFFAOYSA-N 0.000 claims 1
• NHNFADVKRWCCDK-UHFFFAOYSA-N 2-[7-[(4-chloro-2-methylpyrazol-3-yl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=C(N(N=C1)C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N NHNFADVKRWCCDK-UHFFFAOYSA-N 0.000 claims 1
• IDGNVBDQHNQVIQ-UHFFFAOYSA-N 2-[7-[(4-fluorophenoxy)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N,N-dimethylacetamide Chemical compound FC1=CC=C(OCC=2N=C3N(C(C=2)=O)C(=C(S3)C)CC(=O)N(C)C)C=C1 IDGNVBDQHNQVIQ-UHFFFAOYSA-N 0.000 claims 1
• GPJOVABZQQDGKB-UHFFFAOYSA-N 2-[7-[(N-ethyl-4-fluoroanilino)methyl]-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-1-(hydroxymethyl)cyclopropane-1-carbonitrile Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CS2)C1C(C1)(C#N)CO GPJOVABZQQDGKB-UHFFFAOYSA-N 0.000 claims 1
• SNRPSUXVFGRUEP-UHFFFAOYSA-N 2-[7-[[(5-chloropyridin-2-yl)-methylamino]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC=1C=CC(=NC=1)N(C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N SNRPSUXVFGRUEP-UHFFFAOYSA-N 0.000 claims 1
• KKDZVHFVHLLFLC-UHFFFAOYSA-N 2-[7-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=C(C=C(C=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N KKDZVHFVHLLFLC-UHFFFAOYSA-N 0.000 claims 1
• IAQFEIVNCGRNLT-UHFFFAOYSA-N 2-[7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC(=O)NC IAQFEIVNCGRNLT-UHFFFAOYSA-N 0.000 claims 1
• AHGYDRWUHPLOMS-UHFFFAOYSA-N 2-[7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylpropanamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C(=O)NC)C AHGYDRWUHPLOMS-UHFFFAOYSA-N 0.000 claims 1
• KKXKZNIUEQTOLJ-UHFFFAOYSA-N 2-[7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N KKXKZNIUEQTOLJ-UHFFFAOYSA-N 0.000 claims 1
• OABQOUQSIOKKAU-UHFFFAOYSA-N 2-[7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)CC(=O)NC OABQOUQSIOKKAU-UHFFFAOYSA-N 0.000 claims 1
• YDDSVEWRIWAPAL-UHFFFAOYSA-N 2-[7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C#N YDDSVEWRIWAPAL-UHFFFAOYSA-N 0.000 claims 1
• XHLOTGSLFPZYIF-UHFFFAOYSA-N 2-[7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)CC)C1C(C1)C#N XHLOTGSLFPZYIF-UHFFFAOYSA-N 0.000 claims 1
• COPXICUPPLIBSY-UHFFFAOYSA-N 2-[7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC(=O)NC COPXICUPPLIBSY-UHFFFAOYSA-N 0.000 claims 1
• UJKRKJCTSAEIIL-UHFFFAOYSA-N 2-[7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanenitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C#N)C UJKRKJCTSAEIIL-UHFFFAOYSA-N 0.000 claims 1
• UGGWANBYPHDGCL-UHFFFAOYSA-N 2-[7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C#N UGGWANBYPHDGCL-UHFFFAOYSA-N 0.000 claims 1
• ZFBYEBLMJNCSSB-UHFFFAOYSA-N 2-[7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)C1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)CC(=O)NC ZFBYEBLMJNCSSB-UHFFFAOYSA-N 0.000 claims 1
• VIEPCEIHPPWOOS-UHFFFAOYSA-N 2-[7-[[5-bromo-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound BrC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N)C(F)(F)F VIEPCEIHPPWOOS-UHFFFAOYSA-N 0.000 claims 1
• OCBXXTMCQRGCPY-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)CC)C1C(C1)C#N)C(F)(F)F OCBXXTMCQRGCPY-UHFFFAOYSA-N 0.000 claims 1
• MTCONKPBBSQCJJ-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC(=O)NC)C(F)(F)F MTCONKPBBSQCJJ-UHFFFAOYSA-N 0.000 claims 1
• CHAWHADFPAZLJC-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC#N)C(F)(F)F CHAWHADFPAZLJC-UHFFFAOYSA-N 0.000 claims 1
• SQALNDKGODGXJT-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N)C(F)(F)F SQALNDKGODGXJT-UHFFFAOYSA-N 0.000 claims 1
• YGRFJPGSNXMFBF-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]propanenitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C#N)C)C(F)(F)F YGRFJPGSNXMFBF-UHFFFAOYSA-N 0.000 claims 1
• FTIBNGABJNFFAI-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C#N)C(F)(F)F FTIBNGABJNFFAI-UHFFFAOYSA-N 0.000 claims 1
• NXHCPFQAFOSKDD-UHFFFAOYSA-N 2-[7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-6-fluoro-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1F)=O)C(=C(S2)C(F)(F)F)C1C(C1)C#N)C(F)(F)F NXHCPFQAFOSKDD-UHFFFAOYSA-N 0.000 claims 1
• NTONZUGNOSVRSX-UHFFFAOYSA-N 2-[7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC(=O)NC)C(F)(F)F NTONZUGNOSVRSX-UHFFFAOYSA-N 0.000 claims 1
• WNQLSNUKYUYPIF-UHFFFAOYSA-N 2-[7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)CC(=O)NC)C(F)(F)F WNQLSNUKYUYPIF-UHFFFAOYSA-N 0.000 claims 1
• LNFQBSCETUUDEP-UHFFFAOYSA-N 2-[7-[[5-methoxy-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound COC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N)C(F)(F)F LNFQBSCETUUDEP-UHFFFAOYSA-N 0.000 claims 1
• OJNXMBGESFWXNI-UHFFFAOYSA-N 2-[7-[[ethyl-(5-fluoropyridin-2-yl)amino]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]cyclopropane-1-carbonitrile Chemical compound C(C)N(C1=NC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C#N OJNXMBGESFWXNI-UHFFFAOYSA-N 0.000 claims 1
• WJROPMIOTKZXKB-UHFFFAOYSA-N 2-acetyl-7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)(=O)C1=C(N2C(=NC(=CC2=O)CN2N=C(C=C2C(F)(F)F)Cl)S1)C(=O)NCC WJROPMIOTKZXKB-UHFFFAOYSA-N 0.000 claims 1
• FTBJRLQUIASBEV-UHFFFAOYSA-N 2-acetyl-7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)(=O)C1=C(N2C(=NC(=CC2=O)CN2N=C(C=C2Cl)C(F)(F)F)S1)C(=O)NCC FTBJRLQUIASBEV-UHFFFAOYSA-N 0.000 claims 1
• BHTIQSUVHUPABE-UHFFFAOYSA-N 2-chloro-7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-3-(2-methylcyclopropyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=C(N2C(=NC(=CC2=O)CC2=C(C(=CC=C2)C(F)(F)F)F)S1)C1C(C1)C BHTIQSUVHUPABE-UHFFFAOYSA-N 0.000 claims 1
• VGCAFQQCMLPJGN-UHFFFAOYSA-N 2-cyano-N-ethyl-7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C1=C(N2C(=NC(=CC2=O)CC2=C(C(=CC=C2)C(F)(F)F)F)S1)C(=O)NCC VGCAFQQCMLPJGN-UHFFFAOYSA-N 0.000 claims 1
• RUSQSJGEQRGFFW-UHFFFAOYSA-N 2-cyclopropyl-7-[(4-fluorophenoxy)methyl]-N-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C1(CC1)C1=C(N2C(=NC(=CC2=O)COC2=CC=C(C=C2)F)S1)C(=O)NC RUSQSJGEQRGFFW-UHFFFAOYSA-N 0.000 claims 1
• UKLMWMGCQRYYNX-UHFFFAOYSA-N 2-cyclopropyl-7-[(N-ethyl-4-fluoroanilino)methyl]-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=C(N2C(=NC(=CC2=O)CN(C2=CC=C(C=C2)F)CC)S1)C=1C=NC=NC=1 UKLMWMGCQRYYNX-UHFFFAOYSA-N 0.000 claims 1
• ZRZPBCNIOKPJKK-UHFFFAOYSA-N 2-ethoxy-N-ethyl-7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)OC1=C(N2C(=NC(=CC2=O)CC2=C(C(=CC=C2)C(F)(F)F)F)S1)C(=O)NCC ZRZPBCNIOKPJKK-UHFFFAOYSA-N 0.000 claims 1
• OGLXHRJFLFPSQA-UHFFFAOYSA-N 2-ethyl-7-[(N-ethyl-4-fluoroanilino)methyl]-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(CC)sc2n1)-c1cncnc1)c1ccc(F)cc1 OGLXHRJFLFPSQA-UHFFFAOYSA-N 0.000 claims 1
• PNMXVBLESWMMON-UHFFFAOYSA-N 2-ethyl-7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-N-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)C1=C(N2C(=NC(=CC2=O)CC2=C(C(=CC=C2)C(F)(F)F)F)S1)C(=O)NC PNMXVBLESWMMON-UHFFFAOYSA-N 0.000 claims 1
• TWKYFFUEPWSTMP-UHFFFAOYSA-N 2-fluoro-3-[(2-methyl-5-oxo-3-propanoyl-[1,3]thiazolo[3,2-a]pyrimidin-7-yl)methyl]benzonitrile Chemical compound FC1=C(C#N)C=CC=C1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(CC)=O TWKYFFUEPWSTMP-UHFFFAOYSA-N 0.000 claims 1
• FTSYLPLHCKMVBP-UHFFFAOYSA-N 2-fluoro-3-[(2-methyl-5-oxo-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-7-yl)methyl]benzonitrile Chemical compound Cc1sc2nc(Cc3cccc(C#N)c3F)cc(=O)n2c1-c1cncnc1 FTSYLPLHCKMVBP-UHFFFAOYSA-N 0.000 claims 1
• BQRQZEDSHDIXFW-UHFFFAOYSA-N 2-fluoro-3-[[2-methyl-3-(2-methylcyclopropyl)-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound CC1CC1c1c(C)sc2nc(Cc3cccc(C#N)c3F)cc(=O)n12 BQRQZEDSHDIXFW-UHFFFAOYSA-N 0.000 claims 1
• UHRUUTFVPIEAKC-UHFFFAOYSA-N 2-fluoro-3-[[2-methyl-5-oxo-3-[2-(trifluoromethyl)cyclopropyl]-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound FC1=C(C#N)C=CC=C1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C(F)(F)F UHRUUTFVPIEAKC-UHFFFAOYSA-N 0.000 claims 1
• QCLSQGPKTREYCJ-UHFFFAOYSA-N 2-fluoro-3-[[3-(2-methylcyclopropyl)-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound FC1=C(C#N)C=CC=C1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C QCLSQGPKTREYCJ-UHFFFAOYSA-N 0.000 claims 1
• BUVNZZIXNQMJOR-DZGCQCFKSA-N 2-fluoro-5-[[3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]benzonitrile Chemical compound Cc1sc2nc(Cc3ccc(F)c(c3)C#N)cc(=O)n2c1[C@@H]1C[C@H]1CO BUVNZZIXNQMJOR-DZGCQCFKSA-N 0.000 claims 1
• TUZKKRCAJDFAPC-UHFFFAOYSA-N 2-methyl-3-pyrimidin-5-yl-7-[[3-(trifluoromethyl)phenyl]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cc3cccc(c3)C(F)(F)F)cc(=O)n2c1-c1cncnc1 TUZKKRCAJDFAPC-UHFFFAOYSA-N 0.000 claims 1
• XAKADGPJFJDRGH-UHFFFAOYSA-N 2-methyl-3-pyrimidin-5-yl-7-[[5-(trifluoromethyl)pyrazol-1-yl]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nccc3C(F)(F)F)cc(=O)n2c1-c1cncnc1 XAKADGPJFJDRGH-UHFFFAOYSA-N 0.000 claims 1
• CFDIASCTBOBBCN-UHFFFAOYSA-N 2-methyl-7-[[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1cc(nn1Cc1cc(=O)n2c(c(C)sc2n1)-c1cncnc1)C(F)(F)F CFDIASCTBOBBCN-UHFFFAOYSA-N 0.000 claims 1
• IYGUJMGBMBUVGX-UHFFFAOYSA-N 3-(1,2-dihydroxyethyl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C(O)CO)c(C)sc2n1)c1ccc(F)cc1 IYGUJMGBMBUVGX-UHFFFAOYSA-N 0.000 claims 1
• ASRJFVCAATYYFW-UHFFFAOYSA-N 3-(2-aminopyridin-3-yl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cccnc1N)c1ccc(F)cc1 ASRJFVCAATYYFW-UHFFFAOYSA-N 0.000 claims 1
• ZGCVYIURXAWZHC-UHFFFAOYSA-N 3-(2-aminopyridin-4-yl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccnc(N)c1)c1ccc(F)cc1 ZGCVYIURXAWZHC-UHFFFAOYSA-N 0.000 claims 1
• STSVDMGTANHCSD-UHFFFAOYSA-N 3-(2-chloropyridin-3-yl)-7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NC=CC=C1C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1C(F)(F)F)Cl)=O)C STSVDMGTANHCSD-UHFFFAOYSA-N 0.000 claims 1
• FMJDFJHSGXCLGZ-UHFFFAOYSA-N 3-(2-chloropyridin-3-yl)-7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NC=CC=C1C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O)C FMJDFJHSGXCLGZ-UHFFFAOYSA-N 0.000 claims 1
• XXEZXKNYVLZGFK-UHFFFAOYSA-N 3-(2-hydroxypropan-2-yl)-2-methyl-7-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound OC(C)(C)C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1)C(F)(F)F)=O)C XXEZXKNYVLZGFK-UHFFFAOYSA-N 0.000 claims 1
• QPBYRSCGOXHVSY-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cc(F)cc(F)c1)c1ccc(F)cc1 QPBYRSCGOXHVSY-UHFFFAOYSA-N 0.000 claims 1
• ZDKPJPACRBAMFD-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-7-[[(5-chloropyridin-2-yl)-methylamino]methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cncc(Cl)c1)c1ccc(Cl)cn1 ZDKPJPACRBAMFD-UHFFFAOYSA-N 0.000 claims 1
• IIXUXJRUYYODTM-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC=1C=C(C=NC=1)C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O)C(F)(F)F IIXUXJRUYYODTM-UHFFFAOYSA-N 0.000 claims 1
• CQTAIHMUJCFQJN-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC=1C=C(C=NC=1)C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O)C CQTAIHMUJCFQJN-UHFFFAOYSA-N 0.000 claims 1
• GAUDSNSHLNJEDU-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccc(N)nc1)c1ccc(F)cc1 GAUDSNSHLNJEDU-UHFFFAOYSA-N 0.000 claims 1
• KSTCJJIDERNFND-UHFFFAOYSA-N 3-(azetidin-1-ylmethyl)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(CC1=CC(=O)N2C(SC(C)=C2CN2CCC2)=N1)C1=CC=C(F)C=C1 KSTCJJIDERNFND-UHFFFAOYSA-N 0.000 claims 1
• TVPQZXSBCBELBG-UHFFFAOYSA-N 3-(azetidine-1-carbonyl)-7-[(4-fluorophenoxy)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound N1(CCC1)C(=O)C1=C(SC=2N1C(C=C(N=2)COC1=CC=C(C=C1)F)=O)C TVPQZXSBCBELBG-UHFFFAOYSA-N 0.000 claims 1
• JHCACWUNXHHQEL-UHFFFAOYSA-N 3-(cyclopropanecarbonyl)-7-[(4-fluorophenoxy)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C(=O)C1=C(SC=2N1C(C=C(N=2)COC1=CC=C(C=C1)F)=O)C JHCACWUNXHHQEL-UHFFFAOYSA-N 0.000 claims 1
• ZRSVFQYEFHUQSY-UHFFFAOYSA-N 3-(dimethylamino)-7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(CC1=CC(=O)N2C(SC(C)=C2N(C)C)=N1)C1=CC=C(F)C=C1 ZRSVFQYEFHUQSY-UHFFFAOYSA-N 0.000 claims 1
• XHIAMORUQFYLAM-SWLSCSKDSA-N 3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-7-[[3-(trifluoromethyl)phenyl]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cc3cccc(c3)C(F)(F)F)cc(=O)n2c1[C@@H]1C[C@H]1CO XHIAMORUQFYLAM-SWLSCSKDSA-N 0.000 claims 1
• YXRGWFRPQMEBRP-GXSJLCMTSA-N 3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-7-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound OC[C@H]1[C@@H](C1)C1=C(SC=2N1C(C=C(N=2)CN1N=C(C=C1)C(F)(F)F)=O)C YXRGWFRPQMEBRP-GXSJLCMTSA-N 0.000 claims 1
• SFUKARYDWXVCCB-XHDPSFHLSA-N 3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-7-[[4-(trifluoromethyl)phenoxy]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound OC[C@H]1[C@@H](C1)C1=C(SC=2N1C(C=C(N=2)COC1=CC=C(C=C1)C(F)(F)F)=O)C SFUKARYDWXVCCB-XHDPSFHLSA-N 0.000 claims 1
• YLKUJBYDVQGFCM-DZGCQCFKSA-N 3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-7-(indazol-1-ylmethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3ncc4ccccc34)cc(=O)n2c1[C@@H]1C[C@H]1CO YLKUJBYDVQGFCM-DZGCQCFKSA-N 0.000 claims 1
• LNUPJSVXXDVSMX-MAUKXSAKSA-N 3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-7-(isoquinolin-4-ylmethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cc3cncc4ccccc34)cc(=O)n2c1[C@@H]1C[C@H]1CO LNUPJSVXXDVSMX-MAUKXSAKSA-N 0.000 claims 1
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• BCHIUDUYGIQBPU-UHFFFAOYSA-N 5-chloro-1-[[3-(2-methylcyclopropyl)-5-oxo-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-7-yl]methyl]pyrazole-3-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C)C#N BCHIUDUYGIQBPU-UHFFFAOYSA-N 0.000 claims 1
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• NCCCDEXKWZQMLA-UHFFFAOYSA-N 7-(3-bicyclo[4.2.0]octa-1(6),2,4-trienylmethyl)-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3ccc4CCc4c3)cc(=O)n12 NCCCDEXKWZQMLA-UHFFFAOYSA-N 0.000 claims 1
• YUEVMWXTENFCIV-UHFFFAOYSA-N 7-[(2,3-difluorophenyl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound FC1=C(CC=2N=C3N(C(C=2)=O)C(=C(S3)C)C(=O)NCC)C=CC=C1F YUEVMWXTENFCIV-UHFFFAOYSA-N 0.000 claims 1
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• BHRHTYZULMPJBI-UHFFFAOYSA-N 7-[(5-chloropyrazol-1-yl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC BHRHTYZULMPJBI-UHFFFAOYSA-N 0.000 claims 1
• RYIDVFOOFYJBGX-UHFFFAOYSA-N 7-[(5-chloropyridin-2-yl)oxymethyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC=1C=CC(=NC=1)OCC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC RYIDVFOOFYJBGX-UHFFFAOYSA-N 0.000 claims 1
• UVDUHADZLZCIGC-UHFFFAOYSA-N 7-[(5-cyano-2-cyclopropylphenyl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cc(ccc3C3CC3)C#N)cc(=O)n12 UVDUHADZLZCIGC-UHFFFAOYSA-N 0.000 claims 1
• YVMVALPFWNRTPG-UHFFFAOYSA-N 7-[(5-cyano-3-cyclopropyl-2-fluorophenyl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=C(C(=C(C=1)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC)F)C1CC1 YVMVALPFWNRTPG-UHFFFAOYSA-N 0.000 claims 1
• CXEOHZFOUFLDCS-DZGCQCFKSA-N 7-[(5-cyclopropyl-3-methylpyrazol-1-yl)methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)[C@H]1[C@@H](C1)CO)C CXEOHZFOUFLDCS-DZGCQCFKSA-N 0.000 claims 1
• JSNYUERYQXEOON-UHFFFAOYSA-N 7-[(5-cyclopropyltriazol-1-yl)methyl]-3-[2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=CN=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)CO JSNYUERYQXEOON-UHFFFAOYSA-N 0.000 claims 1
• QTAKWTLDBKQPHE-UHFFFAOYSA-N 7-[(5-ethyl-1,3-benzoxazol-6-yl)methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)C=1C(=CC2=C(N=CO2)C=1)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC QTAKWTLDBKQPHE-UHFFFAOYSA-N 0.000 claims 1
• BOHGXGVJUZIQHH-UHFFFAOYSA-N 7-[(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC1Cc2cc(F)ccc2N1Cc1cc(=O)n2c(c(C)sc2n1)-c1cncnc1 BOHGXGVJUZIQHH-UHFFFAOYSA-N 0.000 claims 1
• OFJHWJAWLWGGCV-UHFFFAOYSA-N 7-[(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound CC1Cc2cc(F)ccc2N1Cc1cc(=O)n2c(C#N)c(C)sc2n1 OFJHWJAWLWGGCV-UHFFFAOYSA-N 0.000 claims 1
• PNNISEUNCVYUNK-UHFFFAOYSA-N 7-[(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)methyl]-3-(furan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC1Cc2cc(F)ccc2N1Cc1cc(=O)n2c(c(C)sc2n1)-c1ccco1 PNNISEUNCVYUNK-UHFFFAOYSA-N 0.000 claims 1
• GWZFWCOBJOHUIW-SWLSCSKDSA-N 7-[(5-fluoroindazol-1-yl)methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3ncc4cc(F)ccc34)cc(=O)n2c1[C@@H]1C[C@H]1CO GWZFWCOBJOHUIW-SWLSCSKDSA-N 0.000 claims 1
• WUYZRGURXFHFRG-GXFFZTMASA-N 7-[(5-fluoropyridin-2-yl)oxymethyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(COc3ccc(F)cn3)cc(=O)n2c1[C@@H]1C[C@H]1CO WUYZRGURXFHFRG-GXFFZTMASA-N 0.000 claims 1
• ROSAENWRQPDTTG-UHFFFAOYSA-N 7-[(6-cyanopyridin-2-yl)methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cccc(n3)C#N)cc(=O)n12 ROSAENWRQPDTTG-UHFFFAOYSA-N 0.000 claims 1
• GLGGXCNWOUZMPF-SWLSCSKDSA-N 7-[(6-fluoroindazol-1-yl)methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3ncc4ccc(F)cc34)cc(=O)n2c1[C@@H]1C[C@H]1CO GLGGXCNWOUZMPF-SWLSCSKDSA-N 0.000 claims 1
• QVVRRVXYJKYVRG-UHFFFAOYSA-N 7-[(N-ethyl-3,4-difluoroanilino)methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cncnc1)c1ccc(F)c(F)c1 QVVRRVXYJKYVRG-UHFFFAOYSA-N 0.000 claims 1
• VBPPKTORRRGTRF-UHFFFAOYSA-N 7-[(N-ethyl-3,5-difluoroanilino)methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound CCN(CC1=CC(=O)N2C(SC(C)=C2C#N)=N1)C1=CC(F)=CC(F)=C1 VBPPKTORRRGTRF-UHFFFAOYSA-N 0.000 claims 1
• IHEUFWHPEVLYKM-UHFFFAOYSA-N 7-[(N-ethyl-3-fluoroanilino)methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cncnc1)c1cccc(F)c1 IHEUFWHPEVLYKM-UHFFFAOYSA-N 0.000 claims 1
• VMUSKYDWJGLXNZ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(1,3-oxazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C1)=O)C(=C(S2)C)C=2OC=CN2 VMUSKYDWJGLXNZ-UHFFFAOYSA-N 0.000 claims 1
• YLEMOCWZHWZLPI-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(1,3-thiazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1nccs1)c1ccc(F)cc1 YLEMOCWZHWZLPI-UHFFFAOYSA-N 0.000 claims 1
• IXXGIGYUWDZWED-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(1-methylpyrazol-3-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccn(C)n1)c1ccc(F)cc1 IXXGIGYUWDZWED-UHFFFAOYSA-N 0.000 claims 1
• SDVHRFMWAVMIKF-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(1-methylpyrazol-4-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cnn(C)c1)c1ccc(F)cc1 SDVHRFMWAVMIKF-UHFFFAOYSA-N 0.000 claims 1
• RUXSZXYNLDBKDI-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(1H-pyrazol-4-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(-c3cn[nH]c3)c(C)sc2n1)c1ccc(F)cc1 RUXSZXYNLDBKDI-UHFFFAOYSA-N 0.000 claims 1
• GQLHELLXKQLTCQ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(4-methyl-1,3-thiazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1nc(C)cs1)c1ccc(F)cc1 GQLHELLXKQLTCQ-UHFFFAOYSA-N 0.000 claims 1
• OHUVDRPUEDHBKY-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(6-oxa-1-azaspiro[3.3]heptan-1-ylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CN3CCC33COC3)c(C)sc2n1)c1ccc(F)cc1 OHUVDRPUEDHBKY-UHFFFAOYSA-N 0.000 claims 1
• QUQXRMTXJHHEOP-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(6-oxo-1H-pyridin-3-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccc(=O)[nH]c1)c1ccc(F)cc1 QUQXRMTXJHHEOP-UHFFFAOYSA-N 0.000 claims 1
• BIXNPCRYGBWNPH-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(methylsulfanylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CSC)c(C)sc2n1)c1ccc(F)cc1 BIXNPCRYGBWNPH-UHFFFAOYSA-N 0.000 claims 1
• LCVMDNPQCLLTQH-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-(pyrrolidin-1-ylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CN3CCCC3)c(C)sc2n1)c1ccc(F)cc1 LCVMDNPQCLLTQH-UHFFFAOYSA-N 0.000 claims 1
• PGZJMPQBYBDBNQ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-[5-(trifluoromethyl)pyridin-3-yl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1C=NC=C(C=1)C(F)(F)F PGZJMPQBYBDBNQ-UHFFFAOYSA-N 0.000 claims 1
• VBWIZHLOLJMCIE-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-methylsulfonyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)S(C)(=O)=O)c1ccc(F)cc1 VBWIZHLOLJMCIE-UHFFFAOYSA-N 0.000 claims 1
• JSWZHXCILQSEFM-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-prop-1-en-2-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C(C)=C)c(C)sc2n1)c1ccc(F)cc1 JSWZHXCILQSEFM-UHFFFAOYSA-N 0.000 claims 1
• JUNSLXLVVHCKGV-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-prop-1-ynyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(C#CC)c(C)sc2n1)c1ccc(F)cc1 JUNSLXLVVHCKGV-UHFFFAOYSA-N 0.000 claims 1
• LDKZXKISIQVERJ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-pyridin-4-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C1)=O)C(=C(S2)C)C2=CC=NC=C2 LDKZXKISIQVERJ-UHFFFAOYSA-N 0.000 claims 1
• AZNNRZYGRGVMDL-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-pyrrolidin-1-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(N3CCCC3)c(C)sc2n1)c1ccc(F)cc1 AZNNRZYGRGVMDL-UHFFFAOYSA-N 0.000 claims 1
• YRMCTUIQAOIDCR-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-thiophen-2-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cccs1)c1ccc(F)cc1 YRMCTUIQAOIDCR-UHFFFAOYSA-N 0.000 claims 1
• KLNGMPAFVJSYCT-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-2-methyl-3-thiophen-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccsc1)c1ccc(F)cc1 KLNGMPAFVJSYCT-UHFFFAOYSA-N 0.000 claims 1
• SEYMPBWYEKGHSU-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(2-fluoropyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1C(=NC=CC=1)F SEYMPBWYEKGHSU-UHFFFAOYSA-N 0.000 claims 1
• FRJYLHXETGDIPK-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(3-hydroxy-3-methylbutyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CCC(C)(C)O FRJYLHXETGDIPK-UHFFFAOYSA-N 0.000 claims 1
• ZOZINDYRMWTRIQ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(5-fluoropyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1C=NC=C(C=1)F ZOZINDYRMWTRIQ-UHFFFAOYSA-N 0.000 claims 1
• IDGNXMSHAFZFFB-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(5-methoxypyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1cncc(OC)c1)c1ccc(F)cc1 IDGNXMSHAFZFFB-UHFFFAOYSA-N 0.000 claims 1
• XNGSQTGFIJCKBB-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(furan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccco1)c1ccc(F)cc1 XNGSQTGFIJCKBB-UHFFFAOYSA-N 0.000 claims 1
• XNYLEZLVBWNTOE-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-(furan-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(c(C)sc2n1)-c1ccoc1)c1ccc(F)cc1 XNYLEZLVBWNTOE-UHFFFAOYSA-N 0.000 claims 1
• YPNQIXCPIOCZIR-BLLLJJGKSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(csc2n1)[C@@H]1C[C@H]1CO)c1ccc(F)cc1 YPNQIXCPIOCZIR-BLLLJJGKSA-N 0.000 claims 1
• OGYLWWSXLNKBKV-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-3-[(2-hydroxyethylamino)methyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCN(Cc1cc(=O)n2c(CNCCO)c(C)sc2n1)c1ccc(F)cc1 OGYLWWSXLNKBKV-UHFFFAOYSA-N 0.000 claims 1
• QUGAOEHDZBIECQ-UHFFFAOYSA-N 7-[(N-ethyl-4-fluoroanilino)methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCN(Cc1cc(=O)n2c(C(=O)NC)c(C)sc2n1)c1ccc(F)cc1 QUGAOEHDZBIECQ-UHFFFAOYSA-N 0.000 claims 1
• PTJCJWWDWUTEGV-UHFFFAOYSA-N 7-[1-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]ethyl]-3-[2-(hydroxymethyl)-1-methylcyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=CC(=NN1C(C)C=1N=C2N(C(C=1)=O)C(=C(S2)C)C1(C(C1)CO)C)C(F)(F)F PTJCJWWDWUTEGV-UHFFFAOYSA-N 0.000 claims 1
• OLAUUVVASOAZAN-UHFFFAOYSA-N 7-[[(3,5-dimethyl-1,2-oxazol-4-yl)-methylamino]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CC1=NOC(=C1N(C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC)C OLAUUVVASOAZAN-UHFFFAOYSA-N 0.000 claims 1
• PRTNGQNFTRKEPO-UHFFFAOYSA-N 7-[[(3-ethoxypyridin-2-yl)-methylamino]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)OC=1C(=NC=CC=1)N(C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC PRTNGQNFTRKEPO-UHFFFAOYSA-N 0.000 claims 1
• MVQJNSUBRYPBHE-UHFFFAOYSA-N 7-[[(5-chloropyridin-2-yl)-ethylamino]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC=1C=CC(=NC=1)N(CC)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC MVQJNSUBRYPBHE-UHFFFAOYSA-N 0.000 claims 1
• URPOLQKUAYWWBG-UHFFFAOYSA-N 7-[[(5-chloropyridin-2-yl)-methylamino]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(CN(C)c3ccc(Cl)cn3)cc(=O)n12 URPOLQKUAYWWBG-UHFFFAOYSA-N 0.000 claims 1
• NDGKOXSISKFEAI-UHFFFAOYSA-N 7-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cc(ccc3Cl)C(F)(F)F)cc(=O)n12 NDGKOXSISKFEAI-UHFFFAOYSA-N 0.000 claims 1
• QSHRZQWEIUVFQO-UHFFFAOYSA-N 7-[[2-cyclopropyl-5-(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cc(ccc3C3CC3)C(F)(F)F)cc(=O)n12 QSHRZQWEIUVFQO-UHFFFAOYSA-N 0.000 claims 1
• DFIYEUUJQAMOEY-UHFFFAOYSA-N 7-[[2-fluoro-3-(fluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cccc(CF)c3F)cc(=O)n12 DFIYEUUJQAMOEY-UHFFFAOYSA-N 0.000 claims 1
• RTPXBWYBGXTJMK-UHFFFAOYSA-N 7-[[2-fluoro-3-(hydroxymethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cccc(CO)c3F)cc(=O)n12 RTPXBWYBGXTJMK-UHFFFAOYSA-N 0.000 claims 1
• LDMRXJSWOQMXSV-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)N1CC2(COC2)C1 LDMRXJSWOQMXSV-UHFFFAOYSA-N 0.000 claims 1
• WUWKPLVRKXKTSS-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-3-(4-methyl-1,2,4-triazol-3-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1=NN=CN1C WUWKPLVRKXKTSS-UHFFFAOYSA-N 0.000 claims 1
• RZVAEHQZZVYFAV-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-3-(methylaminomethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CNCC1=C(C)SC2=NC(CC3=CC=CC(=C3F)C(F)(F)F)=CC(=O)N12 RZVAEHQZZVYFAV-UHFFFAOYSA-N 0.000 claims 1
• JIMUGIKJKUGAPW-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-3-(methylsulfonylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CS(=O)(=O)C JIMUGIKJKUGAPW-UHFFFAOYSA-N 0.000 claims 1
• XDNMMUCBEJAPDB-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC1=C(N2C(S1)=NC(CC1=CC=CC(=C1F)C(F)(F)F)=CC2=O)C1=CN=CN=C1 XDNMMUCBEJAPDB-UHFFFAOYSA-N 0.000 claims 1
• HSLOCPRJOQTHAW-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-N-propan-2-yl-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC(C)C HSLOCPRJOQTHAW-UHFFFAOYSA-N 0.000 claims 1
• CWVBQKTWGVRAQB-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-3-(1H-imidazol-2-ylmethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC=1NC=CN=1 CWVBQKTWGVRAQB-UHFFFAOYSA-N 0.000 claims 1
• RTPPTCZDWRAXEA-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-3-(2-hydroxycyclopropyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)O RTPPTCZDWRAXEA-UHFFFAOYSA-N 0.000 claims 1
• QFMHQMOUYGGDOG-UHFFFAOYSA-N 7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-3-(hydroxymethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cc3cccc(c3F)C(F)(F)F)cc(=O)n2c1CO QFMHQMOUYGGDOG-UHFFFAOYSA-N 0.000 claims 1
• DGTZEAVNCMJVBX-UHFFFAOYSA-N 7-[[3,5-bis(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3C(F)(F)F)C(F)(F)F)cc(=O)n2c1-c1cncnc1 DGTZEAVNCMJVBX-UHFFFAOYSA-N 0.000 claims 1
• KMDIWDYHJGCCOW-UHFFFAOYSA-N 7-[[3,5-di(propan-2-yl)pyrazol-1-yl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)(C)C1=NN(C(=C1)C(C)C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NCC KMDIWDYHJGCCOW-UHFFFAOYSA-N 0.000 claims 1
• IEEGWFUYNIRTDI-UHFFFAOYSA-N 7-[[3-(difluoromethyl)-2-fluorophenyl]methyl]-6-fluoro-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cccc(C(F)F)c3F)c(F)c(=O)n12 IEEGWFUYNIRTDI-UHFFFAOYSA-N 0.000 claims 1
• NTCLQJBJBXIHQI-UHFFFAOYSA-N 7-[[3-(difluoromethyl)-2-fluorophenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3cccc(C(F)F)c3F)cc(=O)n12 NTCLQJBJBXIHQI-UHFFFAOYSA-N 0.000 claims 1
• FYWBECAUOKJAQB-UHFFFAOYSA-N 7-[[3-(difluoromethyl)-2-fluorophenyl]methyl]-N-ethyl-6-fluoro-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound FC(C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1F)=O)C(=C(S2)C)C(=O)NCC)F)F FYWBECAUOKJAQB-UHFFFAOYSA-N 0.000 claims 1
• CRAHZCSELRRANR-CMPLNLGQSA-N 7-[[3-(difluoromethyl)-5-methylpyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC(C1=NN(C(=C1)C)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)[C@H]1[C@@H](C1)CO)F CRAHZCSELRRANR-CMPLNLGQSA-N 0.000 claims 1
• BXPVXNJEALEMIY-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-(difluoromethyl)-N-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)F)C(=O)NCC BXPVXNJEALEMIY-UHFFFAOYSA-N 0.000 claims 1
• FQMBNLINTQTKOZ-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-ethoxy-N-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)OCC)C(=O)NCC FQMBNLINTQTKOZ-UHFFFAOYSA-N 0.000 claims 1
• SWAVQMRPOWHMEA-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-ethyl-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)CC)C=1C=NC=CC=1 SWAVQMRPOWHMEA-UHFFFAOYSA-N 0.000 claims 1
• YHEFROGNCXHBJY-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(1,3-oxazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1OC=CN=1 YHEFROGNCXHBJY-UHFFFAOYSA-N 0.000 claims 1
• VODUWUMKMXWUFS-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(1H-pyrazol-5-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n2c1-c1ccn[nH]1 VODUWUMKMXWUFS-UHFFFAOYSA-N 0.000 claims 1
• YPRIHOXVHJIALG-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(2-methylpropanoyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C(C)C)=O YPRIHOXVHJIALG-UHFFFAOYSA-N 0.000 claims 1
• AGFUSFMMPPWWRJ-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(F)(F)F AGFUSFMMPPWWRJ-UHFFFAOYSA-N 0.000 claims 1
• HWBSMQIZZXZFKO-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-propanoyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCC(=O)c1c(C)sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n12 HWBSMQIZZXZFKO-UHFFFAOYSA-N 0.000 claims 1
• KFPRKPLJXNRVIC-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n2c1-c1cncnc1 KFPRKPLJXNRVIC-UHFFFAOYSA-N 0.000 claims 1
• PNFXBVKBRSCKOL-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C#N PNFXBVKBRSCKOL-UHFFFAOYSA-N 0.000 claims 1
• MMRXJXIBMBMBIH-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1-hydroxyethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C)O MMRXJXIBMBMBIH-UHFFFAOYSA-N 0.000 claims 1
• WLVVJYZATGSDCU-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1-hydroxypropan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(CO)C WLVVJYZATGSDCU-UHFFFAOYSA-N 0.000 claims 1
• DAQILJCPZXBHQS-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-hydroxypropan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C)(C)O DAQILJCPZXBHQS-UHFFFAOYSA-N 0.000 claims 1
• KABKRFFYBSVDDL-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-methylcyclopropyl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C KABKRFFYBSVDDL-UHFFFAOYSA-N 0.000 claims 1
• CBLLMZXQCOKPJD-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(5-fluoropyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n2c1-c1cncc(F)c1 CBLLMZXQCOKPJD-UHFFFAOYSA-N 0.000 claims 1
• IVYPHSGBXMWEAD-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)CO IVYPHSGBXMWEAD-UHFFFAOYSA-N 0.000 claims 1
• LLENTLUQLMPYKC-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-cyclobutyl-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1CCC1 LLENTLUQLMPYKC-UHFFFAOYSA-N 0.000 claims 1
• CAZVJUXCGISLMI-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyridin-3-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C=1C=NC=CC=1 CAZVJUXCGISLMI-UHFFFAOYSA-N 0.000 claims 1
• MTSFREDWWZPVMC-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=CS2)C=1C=NC=CC=1 MTSFREDWWZPVMC-UHFFFAOYSA-N 0.000 claims 1
• ORESEAOCYFBZJG-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyrimidin-5-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C=1C=NC=NC=1 ORESEAOCYFBZJG-UHFFFAOYSA-N 0.000 claims 1
• DGBGAANKGSQFMV-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC DGBGAANKGSQFMV-UHFFFAOYSA-N 0.000 claims 1
• QSKDORNKNRCOSM-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methoxy-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(OC)sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n12 QSKDORNKNRCOSM-UHFFFAOYSA-N 0.000 claims 1
• BARZPELKQMUNHN-UHFFFAOYSA-N 7-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cn3nc(Cl)cc3C(F)(F)F)cc(=O)n12 BARZPELKQMUNHN-UHFFFAOYSA-N 0.000 claims 1
• OIEVPKISYQQTRM-UHFFFAOYSA-N 7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound Cc1sc2nc(Cn3nc(cc3C(F)(F)F)C3CC3)cc(=O)n2c1C#N OIEVPKISYQQTRM-UHFFFAOYSA-N 0.000 claims 1
• SWHIQHDDPMKDSH-WCQYABFASA-N 7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C1)=O)C(=C(S2)C)[C@H]2[C@@H](C2)CO SWHIQHDDPMKDSH-WCQYABFASA-N 0.000 claims 1
• JUIRLXJPBZIJIE-UHFFFAOYSA-N 7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methoxy-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(OC)sc2nc(Cn3nc(cc3C(F)(F)F)C3CC3)cc(=O)n12 JUIRLXJPBZIJIE-UHFFFAOYSA-N 0.000 claims 1
• KIPSYTFYGDEEPQ-UHFFFAOYSA-N 7-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cn3nc(cc3C(F)(F)F)C3CC3)cc(=O)n12 KIPSYTFYGDEEPQ-UHFFFAOYSA-N 0.000 claims 1
• BEVRRKVOWZXYIG-UHFFFAOYSA-N 7-[[4,5-difluoro-2-(1,3-oxazol-2-yl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound FC1=CC(=C(C=C1F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC)C=1OC=CN=1 BEVRRKVOWZXYIG-UHFFFAOYSA-N 0.000 claims 1
• OEHYSZMZNXJHDD-UHFFFAOYSA-N 7-[[4,5-difluoro-2-(2-fluoroethyl)phenyl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cc(F)c(F)cc3CCF)cc(=O)n12 OEHYSZMZNXJHDD-UHFFFAOYSA-N 0.000 claims 1
• SSBRFZOUAJQFQE-UHFFFAOYSA-N 7-[[4,5-difluoro-2-(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound FC1=CC(=C(C=C1F)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC)C(F)(F)F SSBRFZOUAJQFQE-UHFFFAOYSA-N 0.000 claims 1
• NTURSWYWWRXBCH-UHFFFAOYSA-N 7-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)c1c(C)sc2nc(Cc3ccc(F)cc3C(F)(F)F)cc(=O)n12 NTURSWYWWRXBCH-UHFFFAOYSA-N 0.000 claims 1
• PCXAHIBDNGGFHL-UHFFFAOYSA-N 7-[[4-fluoro-N-(2,2,2-trifluoroethyl)anilino]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(CN(CC(F)(F)F)c3ccc(F)cc3)cc(=O)n2c1-c1cncnc1 PCXAHIBDNGGFHL-UHFFFAOYSA-N 0.000 claims 1
• UPCMQIKEUIWARO-SUMWQHHRSA-N 7-[[4-fluoro-N-(2-fluoroethyl)anilino]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(CN(CCF)c3ccc(F)cc3)cc(=O)n2c1[C@@H]1C[C@H]1CO UPCMQIKEUIWARO-SUMWQHHRSA-N 0.000 claims 1
• OINFIWKJNSRYQF-UHFFFAOYSA-N 7-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC=1C=CC(=C(C=1)CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC)C(F)(F)F OINFIWKJNSRYQF-UHFFFAOYSA-N 0.000 claims 1
• CVAHEBXTOSKTTQ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-(difluoromethyl)-N-ethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)F)C(=O)NCC)C(F)(F)F CVAHEBXTOSKTTQ-UHFFFAOYSA-N 0.000 claims 1
• HXQZUSKRGPCCPU-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-ethyl-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)CC)C=1C=NC=CC=1)C(F)(F)F HXQZUSKRGPCCPU-UHFFFAOYSA-N 0.000 claims 1
• XEQOYSRKHQAPQB-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methoxy-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)OC)C=1C=NC=CC=1)C(F)(F)F XEQOYSRKHQAPQB-UHFFFAOYSA-N 0.000 claims 1
• ZFMYEPOFHKEQDO-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(1,3-oxazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1OC=CN=1)C(F)(F)F ZFMYEPOFHKEQDO-UHFFFAOYSA-N 0.000 claims 1
• PSXYLGZAJLQYDI-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(1,3-thiazol-2-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n2c1-c1nccs1 PSXYLGZAJLQYDI-UHFFFAOYSA-N 0.000 claims 1
• LEGODGGFRIPPKO-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(1H-pyrazol-5-yl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n2c1-c1ccn[nH]1 LEGODGGFRIPPKO-UHFFFAOYSA-N 0.000 claims 1
• KZMCFVUESRQKIK-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(2,2,2-trifluoroacetyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C(F)(F)F)=O)C(F)(F)F KZMCFVUESRQKIK-UHFFFAOYSA-N 0.000 claims 1
• AVZXUSGJJNROJA-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(2-methylcyclopropyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1C(C1)C)C(F)(F)F AVZXUSGJJNROJA-UHFFFAOYSA-N 0.000 claims 1
• ZNFORCVOZBUUFM-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(2-methylpropanoyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C(C)C)=O)C(F)(F)F ZNFORCVOZBUUFM-UHFFFAOYSA-N 0.000 claims 1
• FUNSMCJLUXYGPO-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(methylsulfonylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CS(=O)(=O)C)C(F)(F)F FUNSMCJLUXYGPO-UHFFFAOYSA-N 0.000 claims 1
• HCPQPEKQYRFLTC-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(pyrazol-1-ylmethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CN1N=CC=C1)C(F)(F)F HCPQPEKQYRFLTC-UHFFFAOYSA-N 0.000 claims 1
• JDHZWRSDTVEODE-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(F)(F)F)C(F)(F)F JDHZWRSDTVEODE-UHFFFAOYSA-N 0.000 claims 1
• QLOXSANVRWADGR-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-prop-1-en-2-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC(=C)c1c(C)sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12 QLOXSANVRWADGR-UHFFFAOYSA-N 0.000 claims 1
• IPQICUVRUDUPJY-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-propanoyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCC(=O)c1c(C)sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12 IPQICUVRUDUPJY-UHFFFAOYSA-N 0.000 claims 1
• WAINMXUAXAZGAX-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n2c1-c1cccnc1 WAINMXUAXAZGAX-UHFFFAOYSA-N 0.000 claims 1
• ZMXDMQPSSRDDMZ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-3-pyrimidin-5-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1C=NC=NC=1)C(F)(F)F ZMXDMQPSSRDDMZ-UHFFFAOYSA-N 0.000 claims 1
• OOKNYSOVTVSTKV-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C#N)C(F)(F)F OOKNYSOVTVSTKV-UHFFFAOYSA-N 0.000 claims 1
• HATVTLYVLITPJX-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1,3-thiazol-4-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound FC(F)(F)C1=NN(CC2=CC(=O)N3C(SC(=C3C3=CSC=N3)C(F)(F)F)=N2)C(Cl)=C1 HATVTLYVLITPJX-UHFFFAOYSA-N 0.000 claims 1
• QKCCTOTZNMHXLM-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1-hydroxyethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C)O)C(F)(F)F QKCCTOTZNMHXLM-UHFFFAOYSA-N 0.000 claims 1
• NEWRCJTUQJYPDO-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1-hydroxypropan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC(CO)c1c(C)sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12 NEWRCJTUQJYPDO-UHFFFAOYSA-N 0.000 claims 1
• ISAXNANEBAXQBF-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1H-imidazol-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1NC=CN=1)C(F)(F)F ISAXNANEBAXQBF-UHFFFAOYSA-N 0.000 claims 1
• HJZIUGASPORNEH-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(1H-pyrazol-5-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1=CC=NN1)C(F)(F)F HJZIUGASPORNEH-UHFFFAOYSA-N 0.000 claims 1
• AXRJJBJRQTXVAQ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)OCC(F)(F)F)C(F)(F)F AXRJJBJRQTXVAQ-UHFFFAOYSA-N 0.000 claims 1
• XDLPHHBTPBWKBE-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-fluoropyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C=1C(=NC=CC=1)F)C(F)(F)F XDLPHHBTPBWKBE-UHFFFAOYSA-N 0.000 claims 1
• URJMIKACZQSXCD-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-hydroxypropan-2-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(C)(C)O)C(F)(F)F URJMIKACZQSXCD-UHFFFAOYSA-N 0.000 claims 1
• UGXOPUOTMVZUFB-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-methylazetidin-1-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)N1C(CC1)C)C(F)(F)F UGXOPUOTMVZUFB-UHFFFAOYSA-N 0.000 claims 1
• DDDKHVRNZUGNLZ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(2-methylcyclopropyl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1C(C1)C)C(F)(F)F DDDKHVRNZUGNLZ-UHFFFAOYSA-N 0.000 claims 1
• AAKIRRZJFYEUNJ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(3-fluoroazetidin-1-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)N1CC(C1)F)C(F)(F)F AAKIRRZJFYEUNJ-UHFFFAOYSA-N 0.000 claims 1
• HRWWIKJTJHTIRC-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(3-methoxyazetidin-1-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)N1CC(C1)OC)C(F)(F)F HRWWIKJTJHTIRC-UHFFFAOYSA-N 0.000 claims 1
• CRKWTVFRMKYZSN-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(5-fluoropyridin-3-yl)-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C=1C=NC=C(C=1)F)C(F)(F)F CRKWTVFRMKYZSN-UHFFFAOYSA-N 0.000 claims 1
• BNONAVIUAYRIOS-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(5-fluoropyridin-3-yl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n2c1-c1cncc(F)c1 BNONAVIUAYRIOS-UHFFFAOYSA-N 0.000 claims 1
• YXYIBLVRPXGSCN-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(cyclopropanecarbonyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)C1CC1)C(F)(F)F YXYIBLVRPXGSCN-UHFFFAOYSA-N 0.000 claims 1
• YUNHLLQMCIWSSZ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(cyclopropylmethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)CC1CC1)C(F)(F)F YUNHLLQMCIWSSZ-UHFFFAOYSA-N 0.000 claims 1
• INKAZIOENVDPIY-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(methoxymethyl)-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)COC)C(F)(F)F INKAZIOENVDPIY-UHFFFAOYSA-N 0.000 claims 1
• RCRRFPRSPRZXCW-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CS2)C(F)(F)F)C(F)(F)F RCRRFPRSPRZXCW-UHFFFAOYSA-N 0.000 claims 1
• BEMABQWYNJVTRG-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n2c1C1CC1CO BEMABQWYNJVTRG-UHFFFAOYSA-N 0.000 claims 1
• OTMAKFFGZVGOTA-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-cyclobutyl-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1CCC1)C(F)(F)F OTMAKFFGZVGOTA-UHFFFAOYSA-N 0.000 claims 1
• WPIDEMHRQUXCBT-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-cyclopropyl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C1CC1)C(F)(F)F WPIDEMHRQUXCBT-UHFFFAOYSA-N 0.000 claims 1
• XACULFLTNACYQS-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-cyclopropyl-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C1CC1)C(F)(F)F XACULFLTNACYQS-UHFFFAOYSA-N 0.000 claims 1
• BFOCGANRFXLEQU-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-methylsulfanyl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)SC)C(F)(F)F BFOCGANRFXLEQU-UHFFFAOYSA-N 0.000 claims 1
• UJACBZKSPOJHBJ-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-prop-1-en-2-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C(=C)C)C(F)(F)F UJACBZKSPOJHBJ-UHFFFAOYSA-N 0.000 claims 1
• QKSSQYMFEBUYKT-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-propanoyl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCC(=O)c1c(sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12)C(F)(F)F QKSSQYMFEBUYKT-UHFFFAOYSA-N 0.000 claims 1
• MAZSPSRHCVMWTN-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyridin-3-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C=1C=NC=CC=1)C(F)(F)F MAZSPSRHCVMWTN-UHFFFAOYSA-N 0.000 claims 1
• WVFKUQHAYHAIAT-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyridin-3-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CS2)C=1C=NC=CC=1)C(F)(F)F WVFKUQHAYHAIAT-UHFFFAOYSA-N 0.000 claims 1
• ZDSJJKKERQQYRG-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyrimidin-5-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)C=1C=NC=NC=1)C(F)(F)F ZDSJJKKERQQYRG-UHFFFAOYSA-N 0.000 claims 1
• ORQDLRKHTOFCLB-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-pyrrolidin-1-yl-2-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C(F)(F)F)N1CCCC1)C(F)(F)F ORQDLRKHTOFCLB-UHFFFAOYSA-N 0.000 claims 1
• SRZSTXBGFWNTPI-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N,2-dimethyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(S2)C)C(=O)NC)C(F)(F)F SRZSTXBGFWNTPI-UHFFFAOYSA-N 0.000 claims 1
• BZQIDNXMKIUMPK-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methoxy-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(OC)sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12 BZQIDNXMKIUMPK-UHFFFAOYSA-N 0.000 claims 1
• MQDBLHZAPZLITE-UHFFFAOYSA-N 7-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cn3nc(cc3Cl)C(F)(F)F)cc(=O)n12 MQDBLHZAPZLITE-UHFFFAOYSA-N 0.000 claims 1
• YICMBEBGNWYZTM-UHFFFAOYSA-N 7-[[5-cyano-2-(2-fluoroethyl)phenyl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cc(ccc3CCF)C#N)cc(=O)n12 YICMBEBGNWYZTM-UHFFFAOYSA-N 0.000 claims 1
• KEIDZUYAMWPTOW-UHFFFAOYSA-N 7-[[5-cyano-2-(trifluoromethyl)phenyl]methyl]-N-ethyl-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)C1=C(C)SC2=NC(CC3=C(C=CC(=C3)C#N)C(F)(F)F)=CC(=O)N12 KEIDZUYAMWPTOW-UHFFFAOYSA-N 0.000 claims 1
• QCUBVPPWVVMNGN-UHFFFAOYSA-N 7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carbonitrile Chemical compound Cc1sc2nc(Cn3nc(cc3C3CC3)C(F)(F)F)cc(=O)n2c1C#N QCUBVPPWVVMNGN-UHFFFAOYSA-N 0.000 claims 1
• OMFVMGAVFXUBGH-WCQYABFASA-N 7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-2-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound Cc1sc2nc(Cn3nc(cc3C3CC3)C(F)(F)F)cc(=O)n2c1[C@@H]1C[C@H]1CO OMFVMGAVFXUBGH-WCQYABFASA-N 0.000 claims 1
• XCQKKHBSCOGLHQ-UHFFFAOYSA-N 7-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-3-[2-(hydroxymethyl)cyclopropyl]-2-propan-2-yl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C1)=O)C(=C(S2)C(C)C)C2C(C2)CO)C(F)(F)F XCQKKHBSCOGLHQ-UHFFFAOYSA-N 0.000 claims 1
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• ZBZNBRLJRWPWRY-UHFFFAOYSA-N N-ethyl-7-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cccc(c3F)C(F)(F)F)cc(=O)n12 ZBZNBRLJRWPWRY-UHFFFAOYSA-N 0.000 claims 1
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• VGSOOLDLVFVOPG-UHFFFAOYSA-N N-ethyl-7-[[5-fluoro-2-(trifluoromethyl)phenyl]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound CCNC(=O)c1c(C)sc2nc(Cc3cc(F)ccc3C(F)(F)F)cc(=O)n12 VGSOOLDLVFVOPG-UHFFFAOYSA-N 0.000 claims 1
• ZWJWFQCNZQWMKO-UHFFFAOYSA-N N-ethyl-7-[[ethyl(pyridin-2-yl)amino]methyl]-2-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-3-carboxamide Chemical compound C(C)NC(=O)C1=C(SC=2N1C(C=C(N=2)CN(C1=NC=CC=C1)CC)=O)C ZWJWFQCNZQWMKO-UHFFFAOYSA-N 0.000 claims 1
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